It’s 2025 now, everyone, and the once far-away-sounding year 2000 is now 25 years behind us. We’re also 25 years into this century.

As the NHL commemorates the quarter-century with their announcement of the Quarter-Century Teams, we figured it was time to revisit what we believe to be the five worst Calgary Flames trades in the last 25 years. It’s impossible to win every deal, meaning every general manager throughout the league is bound to have at least one bad trade on their resume, some former Flames GM’s though, are decorated trade losers.

We’ll count down from five and eventually crown the worst of the worst at one.

Calgary’s trade for Hamonic back in 2017 was both ill-timed and ill-negotiated by former GM Brad Treliving. The Flames were in the upswing stage of their rebuild with young core pieces like Johnny Gaudreau, Sean Monahan, and Sam Bennett beginning to take the mantle and promoting the team from basement-dweller to middle-of-the-pack contender.

At the 2017 draft, Calgary sent a first and two second-round picks to the Islanders for 26-year-old defenceman Travis Hamonic and a fourth-round selection. This deal was an attempt to expedite the rebuild, but instead contributed to the Flames’ perpetual state of “mid.” The team would go on to miss the playoffs in the season following the trade, and over three seasons with Calgary, Hamonic posted 42 points in 193 career games, appearing in just 5 playoff games as a Flame.

In case Flames fans wanted more salt in the wound, that first-round selection was used by the Islanders to select superstar defenceman Noah Dobson. In the end, Calgary grossly overpaid for an asset that they barely even used.

Desperate for cap relief in the 2022 off-season, Calgary traded the oft-injured Sean Monahan along with his $6.38 million cap hit and a conditional first-round selection in 2025 to the Montreal Canadiens for future considerations.

This trade is aggravating for Flames fans on so many levels. First of all, It would be painful to watch a former fan favourite limp out the door for nothing, let alone watching a first-round pick accompany him on his way out. Secondly, Monahan has since had a serious resurgence and it quickly became clear that the Flames had rushed to judgment when they determined that he didn’t have much good hockey left. And lastly, the conditions on the 2025 first still haunt the Flames as there is a legitimate chance they will forfeit their first selection this year.

In the lead-up to the 2013 trade deadline, a failing Flames team traded the face of the franchise, Jarome Iginla, to the Pittsburgh Penguins in exchange for a first-round pick that year and two prospects in Kenny Agostino and Ben Hanowski. This deal was supposed to mark the start of a new era for Calgary, the problem was they didn’t come out of it with any assets.

Hanowski and Agostino both flamed out, no pun intended, each playing just a handful of games for Calgary. They used the first-rounder to select forward Morgan Klimchuk 28th overall, who played just one game with the big club.

Even at the time, the return was considered poor, making this trade one of the worst ever considering the significance of the asset going the other way. The only reason this isn’t higher is because the return is somewhat sizable on paper, which is more than can be said about the next trade.

The Bennett saga is one that no Flames fan wants to relive. Sam was made the highest-drafted Flame of all-time when Calgary selected him fourth overall in 2014. Bennett made his Flame debut the following year and would subsequently be jerked around the lineup for the next 6 seasons, without any consistent role or linemates. Bennett struggled as a result of Calgary’s mismanagement and they eventually decided to move on at the trade deadline in 2021, Sending him and a sixth-rounder to Florida for prospect Emil Heineman and a second-rounder. Bennett immediately flourished with the Panthers and is currently one of the best two-way centres in the league.

What makes this deal worse than Iginla’s is the fact that Bennett was just 26 years old when he was traded, with most of his prime still in front of him. Florida has since climbed to back-to-back Stanley Cup Final appearances, winning the big prize last year, and doing so with Bennett serving as a key cog in their top six.

Here we are, the worst of the worst. I know what you might be thinking, the Flames did get a good return for Tkachuk, bringing back multiple veteran players, a prospect and a first-round selection is not too shabby. It’s the fact that Tkachuk was traded at all that calls into question the competency of Flames management

Treliving seemed unwilling to lock Tkachuk up long-term, and instead bridged him to a three-year deal in 2019. Upon the deal’s expiration, Tkachuk threatened to go to arbitration and become a UFA the following off-season, forcing the Flames to trade him or risk losing him for nothing. Calgary traded Tkachuk and a fourth to Florida on July 22nd, 2022 for MacKenzie Weegar, Jonathan Huberdeau, Cole Schwindt and a 2025 first-rounder. Tkachuk’s departure sunk the Flames back to the bottom of the league a year after winning the Pacific Division. Conversely, the addition of Tkachuk propelled the Panthers to back-to-back cup final appearances in his only two complete years on the team

Weegar and Huberdeau are good players, usually, but there are only a finite number of superstars in the league and it can be incredibly hard to find them, especially when, like Calgary, you never pick in the top three. What makes this the worst of the worst is the fact that Calgary allowed a franchise guy like Tkachuk walk out the door. Other teams have seemingly learned from the Tkachuk debacle in Calgary, locking up their young superstars at the first possible opportunity, regardless of whether or not they’ve proved they’re worthy of an eight year deal

Need more reason to believe that this really is the worst Calgary Flames trade of the last quarter century? Here are some interesting statistics regarding the trade, it was the first time since the Wayne Gretzky trade in 1988 that two 100-point players were traded for each other, Huberdeau then went on to have the highest drop in points season to season of all time (60), going from 115 in 2021-22 to 55 in 2022-23.